Sodium Carbonate → 1-[6-[3-(4-Morpholinyl)-5-nitrophenyl]-2-pyridinyl]cyclobutanol

HRID 2207352ノート

反応式

HRID 2207352 の反応式
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[N:13]=[C:12]([C:14]2([OH:18])[CH2:17][CH2:16][CH2:15]2)[CH:11]=[CH:10][CH:9]=1.[N+:19]([C:22]1[CH:23]=[C:24]([N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)[CH:25]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:27]=1)([O-:21])=[O:20]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[N:37]1([C:24]2[CH:25]=[C:26]([C:8]3[N:13]=[C:12]([C:14]4([OH:18])[CH2:17][CH2:16][CH2:15]4)[CH:11]=[CH:10][CH:9]=3)[CH:27]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=2)[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 589324181-(6-Bromopyridin-2-yl)cyclobutanolHCID 672568704-(3-Nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine

生成物 1

HCID 1180930551-[6-[3-(4-Morpholinyl)-5-nitrophenyl]-2-pyridinyl]cyclobutanol

試薬・触媒・溶媒 1

HCID 178418807HCID 178418807、化合物触媒

反応条件

温度
100 °C

実験手順

Pd(dppf)Cl2-dichloromethane adduct (40.8 mg, 0.05 mmol) and sodium carbonate (2 N, 1.5 mL, 3.0 mmol) were added to 1-(6-bromopyridin-2-yl)cyclobutanol (228 mg, 1.0 mmol) and 4-[3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine (0.2 N in DMF, 5.0 mL, 1.0 mmol) and the reaction mixture was purged and flushed with N2(g) (3×). The reaction mixture was heated to 100° C. for 4 hours, then cooled to room temperature, diluted with water, extracted with diethyl ether, washed with brine, dried over sodium sulfate, filtered an concentrated under reduced pressure. The crude product was purified by silica gel chromatography (ethyl acetate:hexanes) to afford 1-{6-[3-(morpholin-4-yl)-5-nitrophenyl]pyridin-2-yl}cyclobutanol. 1H NMR (500 MHz, CDCl3) δ 8.30-8.23 (m, 1H), 7.98-7.95 (m, 1H), 7.93, (t, J=7.2 Hz 1H), 7.79 (t, J=2.2, 1H), 7.74 (d, J=7.8, 1H), 7.66 (d, J=7.8, 1H), 5.36 (s, 1H), 4.03-3.84 (m, 4H), 3.46-3.29 (m, 4H), 2.82-2.47 (m, 4H), 2.27-2.09 (m, 1H), 2.05-1.91 (m, 1H).

後処理

  1. customthe reaction mixture was purged
  2. customflushed with N2(g) (3×)
  3. temperaturecooled to room temperature
  4. additiondiluted with water
  5. extractionextracted with diethyl ether
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationan concentrated under reduced pressure
  10. customThe crude product was purified by silica gel chromatography (ethyl acetate:hexanes)

出典と根拠

ORDレコード
ord-8764354602794e96b2b97a97ed28a52b
出典データセット
uspto-grants-2016_06
特許番号
US09376418B2

反応ノート

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